Triethylamine → 1-(Benzo[1,2,3]thiadiazole-5-carbonyl)-piperidin-4-one

HRID 1293538

反応式

HRID 1293538 の反応式
C1N=CN(C(N2C=NC=C2)=O)C=1.[S:13]1[C:17]2[CH:18]=[CH:19][C:20]([C:22]([OH:24])=O)=[CH:21][C:16]=2[N:15]=[N:14]1.Cl.[NH:26]1[CH2:31][CH2:30][C:29](=[O:32])[CH2:28][CH2:27]1.C(N(CC)CC)C>C1COCC1.C(OCC)(=O)C>[S:13]1[C:17]2[CH:18]=[CH:19][C:20]([C:22]([N:26]3[CH2:31][CH2:30][C:29](=[O:32])[CH2:28][CH2:27]3)=[O:24])=[CH:21][C:16]=2[N:15]=[N:14]1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 27354581,2,3-Benzothiadiazole-5-carboxylic acidHCID 30848514-Piperidone hydrochloride

生成物 1

HCID 223974651-(Benzo[1,2,3]thiadiazole-5-carbonyl)-piperidin-4-one収率 29.5%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

CDI (4.5 g) added to a solution of the benzo[1,2,3]thiadiazole-5-carboxylic acid (5 g) stirring in THF (100 ml) at RT. After 1 hour 4-piperidone hydrochloride (3.7 g) and triethylamine (4.3 ml) were added and the mixture stirred overnight. The resulting mixture was diluted with ethyl acetate, washed with 2M HCl (100 ml), saturated NaHCO3 solution (200 ml) and then with saturated brine (200 ml). The organic layer was dried (MgSO4) and evaporated to leave a residue which was purified by column chromatography (silica, eluting with mixtures of ethyl acetate in dichloromethane) to give the product as a yellow oil (2.1 g; MS: APCI+(M+H)262).

後処理

  1. washwashed with 2M HCl (100 ml), saturated NaHCO3 solution (200 ml)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customevaporated
  4. customto leave a residue which
  5. customwas purified by column chromatography (silica, eluting with mixtures of ethyl acetate in dichloromethane)

出典と根拠

ORDレコード
ord-5cbbd9b1003a49f3a3a7bfa41754bdf2
出典データセット
uspto-grants-2007_07
特許番号
US07238811B2

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